Abstract
Specific features of the reactions of bis(chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates with 1,3-cyclohexadiene were studied. It was found that the reaction with 2-nitroethenylphosphonate occurs stereoselectively and provides bis(2-chloroethyl) endo-(3-nitrobicyclo[2.2.2]oct-5-en-2-yl)phosphonate. 2-Bromo-2-nitroethenylphosphonate under the same conditions gives a mixture of the endo and exo isomers of the corresponding nitrobicyclooctenes. Enhanced tendency of adducts derived from gem-bromonitroethenyl-phosphonates for intramolecular transformations, such as dehydrohalogenation and aromatization, under the cycloaddition conditions was revealed.
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REFERENCES
Berestovitskaya, V.M., Anisimova, N.A., Litvinov, I.A., Kuzhaeva, A.A., Berkova, G.A., Gubaidullin, A.T., and Deiko, L.I., Zh. Obshch. Khim., 2004, vol. 74, no.4, p. 575.
Kuzhaeva, A.A., Anisimova, N.A., Deiko, L.I., Berkova, G.A., and Berestovitskaya, V.M., Khim. Geterotsikl. Soedin., 2003, no. 8, p. 1264.
Kuzhaeva, A.A., Berestovitskaya, V.M., Deiko, L.I., Anisimova, N.A., and Berkova G.A., Zh. Obshch. Khim., 2002, vol. 72, no.10, p. 1752.
Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes (Conjugated Nitro Compounds), London: Wiley, 1994.
Ono, N., The Nitro Group in Organic Synthesis. Organic Nitro Chem. Ser., New York: VCH, 2001.
Michael, I., Blom, N., and Glintenkamp, L., J. Chem. Soc., Perkin Trans. 1, 1991, no. 8, p. 855.
Ono, N., Kamimura, A., and Kaji, A., J. Org. Chem., 1988, vol. 53, no.2, p. 258.
Emel’yanov, N.P., Azanovskaya, M.M., Romanovskaya, A.P., and Kudryashova, N.D., Dokl. Akad. Nauk BSSR, 1965, vol. 9, no.2, p. 97.
Allen, C.F. and Bell, A., J. Am. Chem. Soc., 1939, vol. 61, p. 521.
Alder, K. and Riekert, H., Justus Liebigs Ann. Chem., 1936, vol. 524, p. 180.
Petrzilka, M. and Grayson, J.I., Synthesis, 1981, no. 10, p. 753.
Gareev, R.D., Loginova, G.M., Zykov, I.N., and Pudovik, A.N., Zh. Obshch. Khim., 1979, vol. 49, no.1, p. 25.
Posner, G.N., Vinander, V., and Afarinkia, K., J. Org. Chem., 1922, vol. 57, no.15, p. 4088.
Wolinsky, J. and Login, R., J. Org. Chem., 1992, vol. 57, no.15, p. 4088.
Ionin, B.I. and Timofeeva, T.N., Usp. Khim., 1972, vol. 41, no.4, p. 758.
Gunther, H., NMR Spectroscopy: An Introduction, Chichester: Wiley, 1980.
Fraser, R.F., Can. J. Chem., 1962, vol. 40, p. 78.
Kas’yan, A.O., Krasnovskaya, O.Yu., Zlenko, E.T., Okovityi, S.I., and Kas’yan, M.I., Zh. Org. Khim., 1996, vol. 32, no.8, p. 1156.
Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983, p. 272.
Baranov, G.M. and Perekalin, V.V., Zh. Obshch. Khim., 1987, vol. 57, no.3, p. 793.
Botata, Zh.E., Deiko, L.I., Kostina, U.L., Baranov, G.M., and Berestovitskaya, V.M., Zh. Obshch. Khim., 1995, vol. 65, no.1, p. 160.
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 387.
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Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 7, 2005, pp. 1106–1110.
Original Russian Text Copyright © 2005 by Anisimova, Kuzhaeva, Berkova, Deiko, Berestovitskaya.
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Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A. et al. Reaction of (2-Nitro- and 2-Bromo-2-nitroethenyl)phosphonates with 1,3-Cyclohexadiene. Russ J Gen Chem 75, 1045–1049 (2005). https://doi.org/10.1007/s11176-005-0365-0
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DOI: https://doi.org/10.1007/s11176-005-0365-0